Cyrus E. Cheslak

        Associate
        Contact Info
        Cyrus E. Cheslak Cyrus E. Cheslak

        Cyrus is a dedicated, hands-on problem-solver who works closely with clients to help them navigate various employment law matters.

        As a member of Verrill’s Labor and Employment Group, Cyrus assists clients with a variety of employment-related matters, including discrimination and harassment claims, employment litigation, and employee relations. He also supports clients in employment counseling matters, including developing and implementing workplace policies and procedures and advising on compliance with evolving legal obligations.

        Drawing on his strong research and writing skills and background in politics, Cyrus approaches each matter in a thoughtful, methodical, and pragmatic way, tailoring his work to align with each client’s operations and goals.

        During law school, Cyrus was a student attorney for the Cumberland County District Attorney’s Office and Cumberland Legal Aid Clinic, and a judicial expert to the Honorable Kermit V. Lipez of the United States Court of Appeals for the First Circuit. He also served as a teaching assistant for the Legal Research & Writing Program and tutored first-year law students, served as Head Case Note & Comment Editor of the Maine Law Review, and competed on Maine Law’s Trial Competition and Moot Court Teams. After graduating magna cum laude from the University of Maine School of Law, Cyrus clerked for The Honorable Thomas E. Humphrey of the Maine Supreme Judicial Court.

        Prior to law school, Cyrus was an aide to United States Senator Susan M. Collins in Washington D.C., where he worked on a variety of legislative matters including health care, agriculture, and nutrition policy, and managed the office’s administrative operations. Cyrus maintains a strong interest in the public policy space.

        Cyrus now lives in Portland with his family and two dogs, where he enjoys hosting backyard barbeques, visiting Maine’s famed breweries, and hiking and exploring Maine’s natural beauty with his kids.

        Services/Industries

        Education

        • University of Maine School of Law (J.D., magna cum laude)
          • Head Case Note & Comment Editor – Maine Law Review
        • Franklin & Marshall College (B.A.)

        Public Service

        • Maine State Bar Association Leadership Academy

        Bar Admissions

        • Maine
        • Massachusetts

        Court and Other Admissions

        • U.S. District Court for the District of Maine

        Memberships

        • Maine State Bar Association
        • Tri-State Defense Lawyers Association
        • Cumberland Bar Association

        Honors

        • Best Brief, Craven Moot Court Competition
        • Faculty Significant Achievement Award
        • Named to New England Super Lawyers Rising Stars list under Civil Litigation: Defense

        Learn more about the third-party ratings, rankings, and selection processes used for inclusion.

        Clerkships

        • Maine Supreme Judicial Court, Justice Humphrey
        Events
        When: October 29, 2026 at 11:00am - 12:00pm ET This Month
        Location: Webinar
        When: August 12, 2026 at 11:00am - 12:00pm ET
        Location: Zoom
        When: June 24, 2026 at 11:00am - 12:00pm
        Location: Webinar

        Firm Highlights

        Blog

        Working 9 to 5? It’s a Way to Make a Livin’, so Make Sure You’re Payin’ for Every Minute: A Maine Employer’s Guide to Stacked Wage & Hour Rules

        Four decades after Dolly Parton gave us both the namesake anthem of the American workday and the film about three fed-up office workers’ dreams of...
        Alerts and Newsletters

        Can AI Pass the Doctor Test? FDA Considers Physician-Inspired Evaluation of GenAI Devices and Other Regulatory Measures

        AI is entering healthcare with indomitable will. It promises to increase efficiency, reduce administrative burden (which healthcare providers so...
        Press Releases

        Verrill Attorney Annabel Rodriguez Named Top Women of Law by Massachusetts Lawyers Weekly

        BOSTON, Massachusetts – Verrill attorney Annabel Rodriguez has been recognized as a Top Women of Law by Massachusetts Lawyers Weekly, and will be...
        Blog

        What Employee Benefits Lawyers Do (and How to Make the Best Use of Us)

        What do employee benefits lawyers do all day and how can clients make the best use of them? This post offers an overview of the kinds of things...
        Media Mentions

        Bloomberg Law Quotes Robert Keach on Expanded Access to Small Business Reorganization

        Verrill attorney Bob Keach was recently featured in Bloomberg Law, discussing legislation that would raise debt limits for bankruptcy relief and...
        Blog

        Phil Bartlett to Step Down as Chair of the Maine Public Utilities Commission

        On September 15, 2026, Governor Janet Mills announced that Phil Bartlett will step down as Chair of the Maine Public Utilities Commission (PUC)...
        Published Works

        Jay McCormack and Michael Fee Co-Author AHLA Article on Skin Substitute Enforcement Trends

        Verrill Partners Jay McCormack and Michael Fee co-authored an article for the American Health Law Association's Fraud and Abuse Practice Group...
        Press Releases

        Verrill Welcomes Health Care & Life Sciences Attorney Elpida Velmahos

        BOSTON, Massachusetts – Verrill is pleased to announce that Elpida Velmahos has joined the firm’s Health Care & Life Sciences Group as an...
        Press Releases

        Verrill Welcomes Litigation & Trial Attorney Emma Pooler

        PORTLAND, Maine – Verrill is pleased to announce that Emma Pooler has joined the firm’s Litigation & Trial Group as an Associate, resident in...
        Published Works

        Four Verrill Attorneys Co-Author Massachusetts Trends and Developments Chapter for Chambers and Partners Child Relocation 2026 Guide

        Verrill attorneys Mary H. Schmidt, Rachel A. Deering, Hannah R. Zukoff, and Mariah G. Tappan co-authored the “Trends and Developments” chapter...
        Blog

        A New Protected Class in Maine: Holders of Final Protection Orders

        In the lead-up to Domestic Violence Awareness Month in October, employers may be taking a closer look at how their policies and practices respond to...
        Alerts and Newsletters

        Verrill Secures SJC Victory for Boston Legacy FC in White Stadium Litigation

        Verrill has secured a significant appellate victory for Boston Legacy FC in the litigation challenging the redevelopment of White Stadium in...